The Melancholy of Gumball Watterson
by The Almighty XDXGX
Summary: The tribulations of one Gumball Watterson Rated M for xXDasXGoochXx
1. I Feel Pretty

I Feel Pretty

By: xXDasXGoochXx

He blinked.

Inhale, exhale.

The blue cat of 14 adjusted the blonde bob wig he had gotten the day before. A small voice in his head pointed out how well the color suited him.

Slightly shaking fingers traced up and down the lightweight fabric that hung from small straps upon his shoulders. the fabric was not one he could define from his meager and near useless knowledge on the world of fashion and clothe-making. what he did know was that the small voice in his head believed the pale yellow color of the sundress suited him.

He had debated for awhile whether it was pertinent to buy shoes - _maybe sandals - _to complete the look he was attempting to achieve, but the sheer overwhelming nervousness that racked his body and his very soul upon his trip to the mall _-a full town over-_ would have totally and utterly consumed him had he returned to buy shoes. The dress had been nearly too much by itself.

Gumball frowned.

He twisted his body to and fro, the small sundress was meant to be for young girls, so it didn't necessarily have darts in it for such things. He traced his hands down the front of the dress, finally coming to the hem of it and slightly stretching it apart and raising it slowly until he could catch a glance of the plain white boy briefs he always had. maybe he could muster up the courage to buy a pair of flower patterned ones. _-Maybe blue…-_

Gumball sighed as he brought a hand up to remove the wig and drop it carefully into the shoebox at his feet. Quickly stripping himself of the dress, he too placed that within the box. Kneeling down to place the top back on he carefully pushed it deep beneath his bed, making sure to cover it with a myriad of old socks and t-shirts.

A bang on the door made him freeze. He quickly got to his feet struggling to redress in his customary jeans and t-shirt.

"Gumball, mom says its time for dinner so hurry up!"

Gumball cursed as he slipped on a stray sock on the ground, tumbling as he struggled to pull his shirt over his head.

"Ah! O-ok! just gimme a sec!"

XDXGX

Dinner was the usual rambunctious affair of his father being messy and loud, his mother giving half hearted attempts to return order and his sister giggling gleefully. Gumball himself smiled and laughed too, although if anyone were to pay attention they would notice the smiles never truly reached his eyes. his mind adrift in confusion, self-loathing, and the ever present fear.

Fear.

He seemed to be full of it these days.

He feared the ostracization that was bound to come if -_when-_ he was found out.

When people found out that he wasn't _Normal_.

Several instances before life and his crazy adventures had allowed him to indulge in his ever growing hobby.

He _liked_ wearing dresses.

In the past he could've easily missed a day of school instead of wearing his mother's wedding dress but the _urge had been too strong._ His _curiosity too strong_. He had outwardly hated and dreaded the fact that he would have to wear a dress but inwardly..._It had been one of the greatest feelings of his young life._ It had been a tragically short experience and his confused yet forever hungry mind weeped at the loss.

Then came his mothers meddling. Situations had sprung together perfectly to gift him the opportunity to taste of the forbidden fruit. He hadn't _needed_ to wear the cheerleading dress in the audition, but it had been _glorious. _

He had wanted to keep the outfit but the fear of being caught saw him toss it shortly after.

Gumball paused in his thoughts as he helped his sister with the dishes after dinner. maybe he could knick a pair of his mom's panties just to give it a try.

a small part of his mind told him the light blue would fit him well.

End?

This was just a small idea i had. I don't know if I will be adding to it further or leaving it as is. Reviews would be appreciated - Marcus B. (xXDasXGoochXx)


	2. I Feel Numb

**I Feel Numb**

**By xXDasXGoochXx**

Gumball stood slouched against a brick wall, eyes half lidded and dull as a midnight draft found purchase beneath his stolen cheerleaders skirt. Currently, he was in East Elmore, a working class part of town that was prevalent with prostitution, gang activities and hard drugs. He was dressed in the white and red cheerleading outfit of his school along with a pair of trainers and one of his mother's strapped purses.

He shivered slightly questioning his judgment of going commando in november. Yet he had discovered during his fifth go at this that underwear just got in the way and would be dirtied anyway. Within the purse was a pack of kleenex for clean up and box cutters for protection. Not that Gumball actually had the mettle to pull a weapon on anyone but it was a good deterrent anyway.

Gumball inwardly sighed, dead dull eyes scanning for potential customers as he thought about the first time he had done this. He had been desperate, the anguish of watching his mother working 3 jobs and taking out horribly bad loans to pay off Anais' medical bills when her kidneys had failed due to a sudden case of Chronic Kidney Disease. Desperate to help in anyway he can he had sold everything of value in a foolish hope to make a enough or just help a little. It had been while on the way home from the hospital late at night that they had driven on the road he currently stood next to due to intensive traffic jams. The road was well known to be high traffic for prostitution, he had stared wide eyed at the scantily clad women walking up and down the block as he passed.

That was when the idea came to him. He had already been practicing crossdressing for months and had gathered a dozen outfits hidden carefully within the old clothes within the attic of his home. He had obviously been extremely apprehensive of the idea. That is, until a week later he had while getting a glass of water late at night, his mother sobbing quietly in the dining room. His mind had been made up at that. The next night, he had donned the shortest skirt he had which had been a cheerleaders outfit he had stolen from school months ago. Donning a blonde wig and snatching one of his mother's strapped purses and a box cutter, Gumball had taken a good long look before leaving. Sneaking out of the house had been easy, taking the late night bus had been easier, only earning a dubious look from the tired looking, overweight bus driver. Once arriving at the bus stop, he had quickly made his way to a corner where he had stood awkwardly for 30 minutes before cursing himself at this stupid idea. He was stopped by a pair of flashing headlights from a dark coloured mini van. Steeling his nerves, he cautiously approached the driver side.

The man driving was a balding guy with large glasses and a sweaty nervous disposition. He rolled down the window and seemed to give Gumball a quick once over.

"Uh um, A-Aren't you a little young miss.."

"Bubble Gum." Gumball curse inwardly. The name just popped in his head. "I'm 18."

Gumball knew the man knew he was lying by the disbelieving look on his face. The man seemed to finally decide, as he began rolling his window up making Gumball's heart drop in his stomach.

"W-wait! I'm 16 ok! I-I just need the money! Y-you've never been with a teenage b-girl before!"

The man stopped at that.

"How much?"

"F-Five Hundred."

"What!? Expensive.."

Gumball swallowed.

"I'm 16 mister. T-tighter than older girls. I-I'll let you stick it in my b-butt.."

Gumball trailed off, cringing inwardly at his own words. The man eyes widened at this before checking his wallet.

"BJ included?"

Gumball nodded reluctantly.

The man unlocked the doors, GUmball taking the cue to hop in, he only hesitated slightly before gripping the purse and hopping in. They drove in silence for five minutes before pulling into a Big Bob's Burger Joint parking lot that was closed and empty.

The man cut the engine before seeming to gather his courage and placing 5 100$ bills on the dashboard.

"Condoms?"

Gumball cursed inwardly.

"Uh N-no need?"

The man's eyes widened.

"Bareback? That's great. B-but first…"

He unzipped himself, Gumball's eyes widening at the large - in his opinion- penis. He hesitated, for a moment, before the sight of a sickly Anais barely hanging on steeled him. He didn't hesitate.

It had been horrible, painful, but mercifully short. He had felt horrible, mentally and physically. Stuffing the money in his purse he had caught the final bus all the while standing as it hurt too much to sit.

It got easier over time. After the fifth, he'd gotten the mouth portion down. After the tenth, the pain had lessened and he had started carrying vaseline. After the 15th, he was simply going through the motions. The twentieth and all he felt was numb, the pain no longer mattering.

He didn't even flinch as the tell tale flashing headlights illuminated briefly. He simply pushed off the wall and sighed, once again steeling himself. This was for Anais, and he would do anything for her...no matter how numb he got.

-End.

**Another Entry to the Melancholy of Gumball Watterson. Read and Review, It pays the bills...Figuratively of course.**


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